Kid-friendly holiday rentals in Monterey

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Popular amenities for Monterey family-friendly rentals

Kid-friendly house rentals

Guest favourite
Home in Becket
4.93 out of 5 average rating, 116 reviews

Beautiful, quiet and cozy home in Becket!

AndrewRating, 5 stars1 month ago
My wife and I stayed here 2 night with our dog and had a great time. The cabin was super cozy and had everything we needed during our stay. Special shoutout to the couch, which was extremely comfortable for late night movie watching! If you are looking for a quiet weekend away to do some hiking, I would certainly recommend staying here. The town of Becket is very rural and food options can be somewhat limited but the house has a full kitchen and grill to use if that's more your style. Overall 5 stars would stay here again.
Top guest favourite
Home in Monterey
5 out of 5 average rating, 21 reviews

Berkshires Retreat | Fenced Yard + Near Tanglewood

CharmaineRating, 5 stars2 months ago
Home is very beautiful. Jim and Susan were very responsive when needed we felt right at home everything was right at our fingertips when needed. We came for a weekend girls getaway and this home helped us achieve that peace we needed. Very spacious we will be back again.
Guest favourite
Home in Monterey
4.88 out of 5 average rating, 78 reviews

- Lake Front 4 Bdr w/ Fast Internet! -

YainaRating, 5 stars3 weeks ago
My family and I loved our stay. Jaryn was a wonderful host and the views from the house were incredible.
Guest favourite
Home in Monterey
4.97 out of 5 average rating, 34 reviews

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

GallianeRating, 5 stars3 months ago
This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.
Guest favourite
Home in Becket
4.96 out of 5 average rating, 26 reviews

New Shaw Pond Skytop Retreat in the Berkshires

NancyRating, 5 stars5 months ago
We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).
Superhost
Home in Monterey
4.88 out of 5 average rating, 8 reviews

Berkshire Ski House on Lake Garfield W/HT By GB

MaryRating, 5 stars4 months ago
This house was great for a winter weekend getaway! Great Barrington, Lenox, and Stockbridge are all adorable towns to visit and are a 15 - 30m drive away. The house itself was cozy and had all the amenities we needed. Shay was very responsive. Something to know about the area is that ride shares and cabs are hard to come by, so having a car that fit everyone we were traveling with was crucial for our group to get around town.
Top guest favourite
Home in Egremont
4.98 out of 5 average rating, 136 reviews

A sunny, quiet chalet beautifully decorated.

CrystalRating, 5 stars2 weeks ago
Great location with easy access to Great Barrington and other Berkshire destinations. Perfect house for families or larger groups, we had everything we needed with various sleeping arrangements. Nice open kitchen and decks. We would be happy to return.
Top guest favourite
Home in Great Barrington
4.98 out of 5 average rating, 114 reviews

Prime location for the best of the Berkshires

ChadRating, 5 stars3 months ago
Marty’s cabin is perfect for a Great Barrington getaway. We stayed in the cabin for a ski weekend, and it simply met all our expectations and then some. The cabin was kept extremely clean and had a ton of extras (board games, coffee, filtered water, etc.) that added a great touch. Location was perfect for a day at butternut mountain. Highly recommend, and will definitely go back next year. Thank you!

Family-friendly apartment rentals

Top guest favourite
Flat in Canaan
4.99 out of 5 average rating, 143 reviews

West Main

CarolineRating, 5 stars2 weeks ago
We stayed here on a weekend trip to Lime Rock and it was a great location! Close to the racetrack and also near the town center, as well as a relatively short drive to Great Barrington. The house was exactly as described and very clean, I would recommend it!
Guest favourite
Flat in Amenia
4.92 out of 5 average rating, 105 reviews

Amenia Main St Cozy Studio

AvocetRating, 5 stars3 weeks ago
Cute, cozy, clean, and super close to the bike trail! Perfect stay for a weekend exploring the towns along the trail.
Top guest favourite
Flat in Hillsdale
4.99 out of 5 average rating, 207 reviews

Serene Suite by Gt. Barrington, Hudson, Tanglewood

EuginaRating, 5 stars3 days ago
We booked last minute to stay for a night to attend an event nearby. While our stay was brief, it was super clean, comfortable, and just what we needed. Everything smelled fresh, and Kelly’s recommendations were helpful too.
Superhost
Flat in Chester
4.77 out of 5 average rating, 202 reviews

Quiet getaway in the Berkshires

GailRating, 5 stars3 weeks ago
Very nice place would stay again joy was very friendly had no problems with the place at all tyvm again joy
Top guest favourite
Flat in Sheffield
4.93 out of 5 average rating, 150 reviews

Private Berkshire Barn Apartment

HelenRating, 5 stars3 weeks ago
Just perfect: cozy, inviting, private. Everything you need, with lots of personal touches. We had a wonderful time!
Top guest favourite
Flat in Petersburgh
4.88 out of 5 average rating, 183 reviews

The Beer Diviner Brewery Apartment

HeidiRating, 5 stars1 week ago
Cindy was great with communications, and gave me all of the instructions I needed to make it a pleasant stay for me, my dog, and the hosts. I stayed Friday and Saturday nights, and enjoyed the craft beer and locally made sourdough pizza in the evenings with a talented musical duo playing on Saturday night. The taproom closes at 8pm, and after closing time the apartment is very quiet and peaceful. The apartment is cozy with attractive furnishings and a comfortable bed, but it is not a place for people with mobility challenges. There are 17 steps up to the apartment, and the shower in a free-standing claw-foot tub doesn't have handrails. I enjoyed my stay, and give it a 5-star review for physically fit singles or a couple!
Guest favourite
Flat in Copake Falls
4.91 out of 5 average rating, 330 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

TimRating, 5 stars2 weeks ago
My wife, dog, and I had a wonderful and peaceful stay at Michael's place. The land is beautiful, the place itself is actually even nicer than the pictures, and there is plenty to do in the area. We will definitely be coming back!
Top guest favourite
Flat in Troy
4.93 out of 5 average rating, 440 reviews

Stunning studio in the heart of Troy: Raven's Den

BobRating, 5 stars1 week ago
Perfect night for a nearby getaway while things done at my apartment. Lot of charm and everything you could need is in this den. Pictures did it justice. I’ll stay again just for the fun of it next time. Igor was easy to communicate with and he was spot on with everything he has posted on the listing. This place is a gem!

Family-friendly apartment rentals

Guest favourite
Apartment in Litchfield County
4.95 out of 5 average rating, 21 reviews

Pacer's Pasture

CerayeRating, 5 stars5 months ago
Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!
Top guest favourite
Apartment in Downtown Hartford
4.99 out of 5 average rating, 126 reviews

Posh Pad in The Business District

KimberlyRating, 5 stars2 weeks ago
We loved our stay at Obi’s apartment in Hartford. It was spacious and comfortable for our family of 4. Street parking was easy. Obi is a great host! We’d love to stay here again the next time we’re in the area.
Guest favourite
Apartment in Lenox
4.97 out of 5 average rating, 34 reviews

Spacious 3 bedroom apt in Lenox historic downtown

JamieRating, 5 stars2 weeks ago
Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!
Superhost
Apartment in New Britain
4.82 out of 5 average rating, 126 reviews

New Britain "Joy of Small Space" Condo

AdamRating, 5 stars1 week ago
Muna was incredible start to finish with my stay. Helpful, communicative and accommodating. Place was perfectly as described. Genuinely recommend a stay at her place!
Guest favourite
Apartment in Albany
4.9 out of 5 average rating, 266 reviews

Elegant, spacious studio apt in historic mansion

LindseyRating, 5 stars1 week ago
Such a unique stay! David gave very helpful instructions for arriving and getting to the property, even supplied photos for extra assistance. The property itself is cozy and in a great part of the city. There’s lots to do nearby, super walkable, and David provides great local recommendations. The shared gallery space was so cool to see too. Great experience!
Superhost
Apartment in Kingston
4.91 out of 5 average rating, 144 reviews

Cozy & walking distance to cafés *spring avails*

JananiRating, 5 stars2 months ago
Cozy apartment, walking distance from the water front. Had a great weekend getaway.
Guest favourite
Apartment in North Adams
4.89 out of 5 average rating, 28 reviews

Downtown Condo - walk to MoCA

RuthRating, 5 stars1 week ago
My husband and I loved our stay at Jo Anne’s place, it was quite,clean private, easy access to parking and very affordable . Stocked with the necessities.
Guest favourite
Apartment in Hancock
4.92 out of 5 average rating, 65 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

MeganRating, 5 stars1 month ago
Very nice spot for one person or a couple. Convenient access to JP base area and amenities. Neat and tidy space, nicely appointed. Great communication from owner.

Quick stats about holiday rentals that are kid-friendly in Monterey

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹7,707 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

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